2.02012-05-31 14:22:19 -06002015-06-03 17:19:06 -0600ECMDB20003M2MDB000852(1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene(1r)-glutathionyl-(2r)-hydroxy-1,2-dihydronaphthalene belongs to the class of Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. (inferred from compound structure)(1R, 2S)-1,2-dihydronaphthalene-1,2-diol(1R,2S)-1,2-dihydro-1,2-dihyroxynaphthalene(1R,2S)-1,2-dihydronaphthalene-1,2-diol(1R,2S)-naphthalene-1,2-dihydrodiol(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-Hydroxy-1,2-dihydronaphthalen-1-ylsulfanyl-1-oxopropan-2-ylamino-5-oxopentanoate(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-ylsulfanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-Hydroxy-1,2-dihydronaphthalen-1-ylsulphanyl-1-oxopropan-2-ylamino-5-oxopentanoate(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-Hydroxy-1,2-dihydronaphthalen-1-ylsulphanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid3,4-dihydronaphthalene-3,4-diol<i>cis</i>-1,2-dihydronaphthalene-1,2-diolcis-1,2-Dihydronaphthalene-1,2-diolCis-1,2-dihydroxy-1,2-dihydronaphthaleneL-g-Glutamyl-S-(1R,2R)-2-hydroxy-1,2-dihydro-1-naphthalenyl-L-cysteinylglycineL-gamma-Glutamyl-S-(1R,2R)-2-hydroxy-1,2-dihydro-1-naphthalenyl-L-cysteinylglycineL-γ-Glutamyl-S-(1R,2R)-2-hydroxy-1,2-dihydro-1-naphthalenyl-L-cysteinylglycineC20H25N3O7S451.493451.141320859(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-{[(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid[H][C@](N)(CCC(O)=N[C@@]([H])(CS[C@]1([H])C2=CC=CC=C2C=C[C@@]1([H])O)C(O)=NCC(O)=O)C(O)=OInChI=1S/C20H25N3O7S/c21-13(20(29)30)6-8-16(25)23-14(19(28)22-9-17(26)27)10-31-18-12-4-2-1-3-11(12)5-7-15(18)24/h1-5,7,13-15,18,24H,6,8-10,21H2,(H,22,28)(H,23,25)(H,26,27)(H,29,30)/t13-,14-,15+,18+/m0/s1UWBZAZWPTVBBEL-OIPACUDHSA-NCytoplasmPeriplasmlogp-1.59logs-3.89solubility5.81e-02 g/llogp-1.7pka_strongest_acidic1.96pka_strongest_basic9.54iupac(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acidaverage_mass451.493mono_mass451.141320859smiles[H][C@](N)(CCC(O)=N[C@@]([H])(CS[C@]1([H])C2=CC=CC=C2C=C[C@@]1([H])O)C(O)=NCC(O)=O)C(O)=OformulaC20H25N3O7SinchiInChI=1S/C20H25N3O7S/c21-13(20(29)30)6-8-16(25)23-14(19(28)22-9-17(26)27)10-31-18-12-4-2-1-3-11(12)5-7-15(18)24/h1-5,7,13-15,18,24H,6,8-10,21H2,(H,22,28)(H,23,25)(H,26,27)(H,29,30)/t13-,14-,15+,18+/m0/s1inchikeyUWBZAZWPTVBBEL-OIPACUDHSA-Npolar_surface_area186.03refractivity114.1polarizability45rotatable_bond_count11acceptor_count10donor_count6physiological_charge-2formal_charge0Glutathione metabolismThe biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a
glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione.
This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione.
PW000833ec00480MetabolicSpecdb::CMs34134Specdb::CMs48123Specdb::CMs156456Specdb::CMs156458Specdb::CMs156460Specdb::CMs156462Specdb::CMs170938Specdb::CMs280113Specdb::NmrOneD56952Specdb::NmrOneD56953Specdb::NmrOneD56954Specdb::NmrOneD56955Specdb::NmrOneD56956Specdb::NmrOneD56957Specdb::NmrOneD56958Specdb::NmrOneD56959Specdb::NmrOneD56960Specdb::NmrOneD56961Specdb::NmrOneD56962Specdb::NmrOneD56963Specdb::NmrOneD56964Specdb::NmrOneD56965Specdb::NmrOneD56966Specdb::NmrOneD56967Specdb::NmrOneD56968Specdb::NmrOneD56969Specdb::NmrOneD56970Specdb::NmrOneD56971Specdb::MsMs29474Specdb::MsMs29475Specdb::MsMs29476Specdb::MsMs36032Specdb::MsMs36033Specdb::MsMs360341195404610128341C14793CIS-12-DIHYDRONAPHTHALENE-12-DIOLKanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Glutathione S-transferaseP0A9D2GST_ECOLIgsthttp://ecmdb.ca/proteins/P0A9D2.xmlGSH-dependent disulfide bond oxidoreductaseP77526yfcGhttp://ecmdb.ca/proteins/P77526.xml(1S,2R)-Naphthalene 1,2-oxide + Glutathione <> (1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthaleneR07003Naphthalene epoxide + Glutathione + (1R,2S)-Naphthalene 1,2-oxide > (1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalenePW_R005206